Issa Rae on Her Leap to TV, Double Standards and Friendship Goals
By Olivia Armstrong
HBO: Now that the season has come to a close, what has the response been like from fans of your web series, Awkward Black Girl?
ISSA RAE: For the most part, they loved it just as much, if not more. I’m glad I’ve been allowed to move on from Awkward Black Girl and give them something new, more grown, and that’s a bit closer to me. It’s been great to see the response. Some have gone back to revisit Awkward Black Girl as a result of Insecure so that’s been amazing, too.
HBO: Were the raps and inner monologues featured on Awkward Black Girl aspects you knew you wanted to keep when moving to TV?
ISSA RAE: I did. I really liked the idea of rap as a device and had a lot of fun writing these trash raps. That, I knew, as a device I didn’t want to let go. Even the fantasy element. I’ve always imagined what I will say or what I could have said but didn’t. I feel like that’s so true to someone who identifies as passive aggressive. You’re always imagining conversations or wishing you said something or said it in a different way than you intended to. So yes, I consciously took those devices to the new show.
HBO: What was one of the more challenging aspects shifting from a web format to a half-hour show?
ISSA RAE: The waiting! I want people to see the show. With Awkward Black Girl, it was like, “I just finished this two seconds ago and you’re seeing it now.” Now I think, it’s waiting for it to be out and being like, “Y’all aren’t even ready for this.” It was agonizing that Episode 1 was released two weeks before when Episode 1 was officially released, which was three weeks before Episode 2, so it’s like, “Ahh, I just want y’all to see it.” When people told me they can’t wait for the next episode, I’m like, “B*tch, you and me both!”
HBO: We meet Issa and Lawrence at a time when they seem to be growing apart. But do you think they still have more in common than they’d maybe like to acknowledge?
ISSA RAE: When you spend five years with someone, you know them in a raw, intimate way. In any relationship, you find new ways to love, understand, and communicate with each other. And unless you’re both actively working on that relationship, it can fade away. You can fall out of love. With Issa and Lawrence; one of them, at any given moment, was working harder than the other to keep the relationship alive. But there was a mistake that was made and it’s moving past that mistake that’s vital for them. Whether or not they decide to, we’ll see.
HBO: Speaking of that mistake. We know why Issa cheats. But rather than an act of revenge, it feels like more of an act of self-discovery. Was it important to have the audience empathize with her in this moment?
ISSA RAE: It was important to have the audience see where she was coming from at the same time they saw Lawrence working on himself. I remember I was writing a script in my early ‘20s where the title character--a woman--cheated and an exec said, “No, the woman cannot cheat. Women cannot come back from cheating. It makes them unlikable.” I remember thinking, “That is so f**king sexist and ridiculous.” What a crazy double standard that men can do that constantly.
I wanted to create an empathetic lead character. Obviously you’re supposed to root for her, but for her to [cheat] when Lawrence is trying to be better for her felt like a very real thing. It’s more about her than it is about him, and to see people so furious and react so viscerally means we’re striking a chord. Everyone knows why she did it, they’re just mad at her for doing it. But they can relate to why. That was definitely important in the [writer’s] room, in our discussions to make sure we made it feel like a very real, conscious decision.
HBO: Lawrence isn’t totally innocent either. Him waiting for Tasha’s teller to become available, and then having lunch with her at the mall. Do you think he’s also curious about who else is out there?
ISSA RAE: He’s seeking something he’s not getting in his own relationship. Tasha provided something for him he desired. He got what he needed from her: that confidence boost to make him better for Issa. I wouldn’t put that on the same level as Issa going out and cheating, but I think they were both seeking something they could have given each other.
HBO: Can we talk about the pivotal moment between Jared and Molly? How did his confession come to fruition in the writer’s room? Is it more important for his story or for Molly’s?
ISSA RAE: I think it was important to just put out there in terms of our generational ideals. It came about because, around ten years ago, I was talking with my girlfriends about dating and said, “If you had told me five years ago that I was dating a guy, and I found out he had been with another guy, I would have immediately been like, “Nah, nuh-uh, hell no, I will not be with you.” There was an ick-factor I couldn’t explain. But I was telling my friends how, now that I’ve become so desensitized and have more gay friends, I don’t think I would mind if I were dating a guy who had been with another guy. And they were like, “Are you f**king serious? That means he’s gay.” I was fascinated by that discussion. I’ve had that [discussion] yearly and seen a lot of my girlfriends still feel the same way--that they could not be with a guy who had experience with other guys.
I’ve always been fascinated with the notion of the double standard of male fluidity, specifically black male fluidity. I wanted to explore that in a very real way. I think it was something for Molly’s story, but it was also--and we try to avoid statements on this show--but it also said, “Well, you think about it. If you were in Molly’s shoes, is she justified?” Putting it in Molly’s point of view, I think we put it out there as a conversation-starter: “What do you feel about it? Is that double standard fair?”
HBO: Shifting gears a bit: can we talk about the music and fashion featured on the show? How did you work to make them such subtle staples of the series?
ISSA RAE: I’m a huge fan of music in television: how it makes you feel and how you tap into a memory. I definitely wanted that to be present in the show. Our music supervisor is Raphael Saadiq and our music consultant is Solange Knowles. Solange--who wanted to have new, L.A. based, female artists featured prominently--was the perfect person to help us. Melina [Matsoukas] also has strong taste and a background in music too, having directed so many music videos with local artists. And Prentice [Penny] is a lover of hip-hop, past and present. We knew the music had to be curated perfectly. We wanted the show to have its own distinct sound.
On the fashion side, I give all credit to our costume designer, Ayanna James. She had a vision and worked closely with Melina, who is heavily into fashion, to figure out the story the wardrobes would tell. For my character, I wanted to it to feel close to me because this is a character who is, for the most part, me. I wanted it to be my basic fashion sense, but hyped. So her vision for my character was every outfit is unique, but there’s always one thing that’s a little bit different. For Molly, it was about tapping into how stylish she is. She’s dressing for the career she wants, for the man that she wants. They were great about communicating that.
HBO: At the end of the finale, we’re left with Issa and Molly facing a new chapter in their lives. Do you think they’re both ready to face themselves?
ISSA RAE: I think they’re ready to face themselves with each other. That’s what’s so important about their friendship. They call each other out and take each other to task. Sometimes you can lie to yourself. Even something as simple as a diet. I remember being like, “I’m on my little healthy eating streak so call me out if I need it,” but not really meaning it. And you have those friends who are like, “Nuh-uh, girl put that doughnut down because you specifically said you were trying to be better.” I think that’s what Molly and Issa do for each other--they try and help each other be better. And sometimes, you don’t want to be called out. Sometimes you’re like, “F**k you, I want this doughnut. Get off my back.” But real friends will call you out and help you be better.
HBO: If there’s one thing about Insecure you hope audiences will take with them, what would it be?
ISSA RAE: I love that people are talking. I want them to talk about how the topics brought up in the show relates to their lives. I want them to keep talking about the characters and see how their lives parallel their own. That’s what brings me joy. That there are group texts and conference calls dedicated to talking about the show, it’s crazy to me and something I never imagined. So for me? Just talk about it.